22-08-21 | Megan Ryder
I have been a closet crossdresser for a lot of years
now and like most cross dressers wish that I had
someone to share it with. Many years ago I had told me
ex wife that I was one and she seemed very supportive
even buying me panties.
However a few months later she filed for divorce and
used my crossdressing as her reason. When I met my
currant wife 15 years ago I was very tempted to tell
her right off to avoid any problems down the road but I
have to admit I chickened out.
My wife and I work opposite shifts so I have a lot of
time to do my dressing while she is at work. I work the
graveyard shift and get home around 7am. I then get her
up and we spend some time together and she is off to
work, At that time I usually slide on my lacy pink
nighty and crawl into bed. Jessie doesn't get home
until around 6:30 so I set my alarm for 5:30 to get
myself up and hide my nighty.
Both of us have Wednesday and Thursday off and last
Wednesday I went thru our usual routine and got Jessie
off to work and crawled into bed wearing my nighty. I
woke up feeling refreshed and looked at the clock on
the wall and it said it was a little after 1.
Fantastic I had several hours to dress and play so I
turned off my alarm and went to my hiding spot to get
my cloths. I have several pair of panties and 3 bras
and 2 nightys but only one regular outfit. I slid on
the red lacy thong panty and matching bra and then the
thigh hi nylons. I love the feeling of nylons. Next I
went to my wives makeup table and did my makeup and
finished buy putting on stick on nails.
I stepped into my black dress that goes to just above
my knees and put on my red wig and after sliding on my
black heels I was done and I felt so nice. I paraded
around the house for a few minutes wishing I could go
outside but was too scared. So I headed to the bedroom
and to my computer to chat with other cross dressers on
line.
I had only been on line about 20 minutes when I heard "
what in the hell is going on" I spun around and Jessie
was standing in the doorway. I looked up at the cock
and it hadn't moved , the batteries were dead. The
clock on the computer read 6:15. Mt heart was about to
pound out of my chest I didn't have any words to say I
attempted to close the chat room I was in but my hands
were shaking to bad. Tears were starting to form in my
eyes.
Jessie walked closer and more quietly again asked what
I was doing. She pulled a chair next to mine and put
her hand on my knee and softly said, "Calm down and
tell me what is going on here."
Nervously I explained to her that I was a cross dresser
and I had been for years. I explained about my ex and
because of that I had been afraid to tell her. She
looked me in the eyes and told me to relax she wasn't
going anywhere and that she wished I had told her
sooner rather than finding out this way. She kissed me
softly and suggested that I go fix us both a drink and
she would change and meet me in the living room to
discuss it more.
Jessie walked out of the bedroom and had changed into a
black dress that barely covered the tops of her nylons
and had a plunging neckline that showed most of her 38D
tits. She sat next to me on the couch and sipped her
drink and started coaching me on the proper way for a
lady to sit and how to walk in my heels. We worked
together and made dinner and sat at the table with more
conversation about my dressing. After we cleared up
dinner she looked at me and said "ok we are going for a
drive." I was very nervous and at first objected but
she insisted. I didn't have a purse for my wallet and
keys so she lent me one telling me that she could see
that tomorrow we were going to have to go shopping to
get me the things a girl had to have.
We just drove around town for about an hour and soon I
was relaxing. She then told me to drive to an adult
book store that we check out regularly. I pulled into
the parking area and she said for us to go inside.
Again I was scared but she pointed out that I was going
to have to get used to it because she wouldn't allow me
to be an at home bitch. We entered the store and was
greeted by the clerk who didn't give me a second look.
There were 4 other guys all looking at magazines.
Jessie headed for the toy rack and told me to go find a
cross dresser magazine I walked over to the magazine
area and all the guys looked at me but only smiled. I
found a CD magazine and met Jessie back at the counter.
She told me to go ahead and go to the car and she would
be there in a minute.
When I stepped into the lot I noticed to of the guys
from the store were standing there talking and they
happened to be right next to my car. As I approached
and deactivated my car alarm the chirping noise made
the 2 look up and see me. As I approached the door one
of the guys reached down and opened the car door for
me. I thanked him as I slid in but what I didn't
realize was that he had been able to see up my skirt.
He smiled at me and said, "I've always liked a lady
with some extra equipment."
Jessie was at the car shortly and told me to head home.
When we got home we made more drinks and sat together
at the couch looking thru the cross dresser magazine
together. After about an hour Jessie told me she was
going to change her cloths .I told her Id change to and
she told me that I should change into my nighty.
I was in my nighty when she walked out o the bathroom
wearing one of my big t shirts and popping out from
under it was a big plastic cock. She put the dildo next
to my lips and told me that since I always liked her to
suck a cock that I had to learn how also. I started by
licking the head of the cock and slowly started taking
it deeper and deeper in my mouth. She kept encouraging
what I was doing and I found myself moaning and making
loud slurping sounds as I sucked.
She told me to stop sucking her cock and to get on my
hands and knees on the edge of the bed. She pulled my
nighty up over my ass and I felt her applying KY gel to
my asshole sliding fingers in me. She then spread it
all over the dildo. She spread my cheeks wide and I
could feel the head of the dildo next to my asshole. I
pushed back to take it but it wouldn't go in.
Jessie was rocking back and forth and with each thrust
the dildo felt like it would go in a bit more until I
felt it break thru and slid in. Slowly she started
pumping my as with it and she began to increase the
pass. Soon she was fucking my ass hard and I was
telling her how good it felt. The door bell rang and I
was wondering who could be at the door at 2 am.
With me in a nighty Jessie told me she would check. A
few minutes later she walked back into the bedroom with
the clerk from the book store. Jessie smiled at me and
said" he thought you looked sexy and he likes a girl
with a cock. She walked to him and started kissing him
and he started feeling her thru the shirt. Her nipples
were getting hard and when she dropped his pants I
couldn't help but star at his huge cock. It was at
least 9 inches and very thick.
I looked at her and told her that there was no way that
cock would go in my ass. She just laughed and said tats
not wear its going. She peeled off her shirt and put
the strap on back on and had me get back on my knees.
She added more KY to my ass and again slowly slid the
dildo in me. The clerk came around so his cock was
inches from my mouth and Jessie told me to suck it, I
took the tip in my mouth and started sucking. He
started working his cock deeper and deeper in my mouth
and I started sucking harder and harder. I grabbed the
shaft and started pumping him as I sucked. Soon I could
taste his pre-cum and it made me go wild I was sucking
and I wanted his cum down my throat.
After a few minutes he announced that he was about to
cum and I felt his hot sticky juice in the back of my
throat. I didn't stop sucking and took every drop. I
continued to gently suck him until his cock went soft a
slid out of my mouth. Jessie then stopped fucking my
ass and we all sat around catching our breath and
chatting.
The clerk got dressed and Jessie walked him back to the
door where they kissed as he played with her tits I met
her at the couch and she was telling me how horny she
was. I sat her on the couch and buried my face in her
cunt. I licked it and nibbled on it until I made her
cum hard. I then had her get on her knees and slid my
cock into her wet pussy and fucked her like never
before. We both cum and collapsed laying there
snuggling.
Jessie took my face and whispered, "See what you have
been missing. If you had told me sooner you would have
enjoyed a lot more of this."
END
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